After 23 years at Microsoft, I chose a transition I knew well professionally and then lived personally.
For most of my career, I worked in people operations, managing the employee lifecycle from hire to retire. I spent years helping people through onboarding, moves, leaves, and exits. I thought that made me well prepared for my own transition.
It didn't.
Knowing the process is not the same as living through it.
Change is external and happens on a date: a role changes, a team reorganizes, a chapter closes. Transition is the psychological process of letting go of who you were in that context, sitting in the uncomfortable in-between, and eventually becoming someone new in a new context.
Organizations are good at managing change. They build timelines, communication plans, and checklists. They are much worse at transition, because it can't be scheduled. People move through it at their own pace, and no plan can rush it.
I've designed change plans for large global workforces. This time I was the one in the middle of the story.
When a long chapter closes, the pull is to fill the space quickly. Update the résumé, say yes to the first good-sounding opportunity, and prove the next chapter measures up to the last one. After two decades with one company, your identity and your employer's name become tangled. A new title feels like the fastest way to untangle them.
But speed is not the same as direction. A fast answer to "what's next?" can quietly recreate the same life, with the same compromises, under a different logo.
So I did the harder thing first. Before I decided what was next, I asked what I valued — and I tried to answer honestly rather than impressively:
What did I do well that gave me energy, and what did I do well that quietly drained me? Competence and fulfillment are not the same thing.
Which of my values were honored in my last role, and which did I set aside? I wanted to name the trade-offs I made, not rationalize them.
What was I carrying that I no longer needed? Some of it was identity, some habit, some other people's expectations.
Who was I when no title was attached? This was the question I found most uncomfortable and most useful.
What would I be proud to say yes to, and what would I be relieved to say no to? Both answers were data.
I use this lens with the people I coach, and I applied it to myself. It's easy to hold space for someone else's uncertainty. It's much harder to hold it for your own.
A value system is only useful if it changes your choices. So I turned mine into criteria I could use when opportunities showed up — whether a role, a project, a board seat, or something I might build myself.
Does this work let me be who I say I am? Does it fit the life I want to be living in five years, or only the résumé I want to have?
Some good opportunities failed that test, and I said no to them. A "no" that comes from clarity is not a loss. It's the point of doing this work.
Honoring who you are doesn't mean throwing away what you've built. My 23 years taught me how to lead through complexity, how to make hard people decisions with care, and how to help organizations move without losing the humans inside them. Those are mine, and they travel with me.
It does mean being honest about what to carry forward and what to leave behind — and giving yourself permission to want something different.
Whether you chose your transition or it arrived without warning, here's what I'd offer:
Name what's ending. Grieving what you're leaving is not weakness. It's what makes room for what comes next.
Resist the rush. Urgency can be real, whether it's financial or just the discomfort of not knowing — but decide what you can afford to take time on, and protect that time.
Write down your values before you read job descriptions. Otherwise the opportunities will define them for you.
Get a thinking partner. Someone who asks good questions and doesn't rush to give answers is worth far more than someone who gives advice.
Whatever sets the date, I got to choose how I moved through what followed — and I did it deliberately. That process led me to my next chapter, and I chose it on purpose.
If you're navigating a transition of your own and want a thinking partner, I'd love to hear from you.